Abstract: This study examines the transfer of first language (L1) and second language (L2) pragmatic expression—realized in the request speech act—in oral and written modalities by Spanish-speaking third language (L3) Portuguese learners (bilingual Spanish heritage speakers, native English speakers who are proficient in L2 Spanish, and native Spanish speakers). Research questions ask if learners differ in the transfer of pragmatic knowledge from the L1 or L2 in an oral versus written modality, and if the three learner groups differ in pragmatic expression in the two modalities. Results indicate that the groups respond differently in the two modalities, showing sensitivity to contextual constraints. Few instances of clear transfer are seen, mostly from Spanish at the single-word level. A picture more complex than Kellerman's hypothesis emerges, addressing creative L3 pragmatic and lexical construction.